Structures and conformations of (–)-isobicyclogermacrenal and (–)-lepidozenal, two key sesquiterpenoids of the cis- and trans-10,3-bicyclic ring systems, from the liverwort Lepidozia vitrea : X-ray crystal structure analysis of the hydroxy derivative of (–)-isobicyclogermacrenal

Structures and conformations of (–)-isobicyclogermacrenal and (–)-lepidozenal, two key sesquiterpenoids of the cis- and trans-10,3-bicyclic ring systems, from the liverwort Lepidozia vitrea : X-ray crystal structure analysis of the hydroxy derivative of (–)-isobicyclogermacrenal

Author

氏名

松尾 昭彦

ヨミ

マツオ アキヒコ

別名

Matsuo Akihiko

氏名

ヨミ

ノザキ ヒロシ

別名

Nozaki Hiroshi

氏名

ヨミ

クボタ ナオジ

別名

Kubota Naoji

氏名

ヨミ

ウト セイリュウ

別名

Uto Seiryû

氏名

ヨミ

ナカヤマ ミツル

別名

Nakayama Mitsuru

Abstract

The structures and absolute configurations of the two sesquiterpene aldehydes, (–)-isobicyclogermacrenal (1) and (–)-lepidozenal (2), which were isolated from the liverwort Lepidozia vitrea, have been determined on the basis of chemical and spectroscopic evidence to be (6R,7S)-6,11-cyclogermacra-1(10)-E,4E-dien-14-al and (6R,7S)-lepidoza-1 (10)E,4E-dien-14-al, consisting of the cis- and trans-10,3-bicyclic ring systems. The structure of the former (1) has been confirmed by a single-crystal X-ray analysis of its hydroxy derivative (7). The molecular conformations, biogenetical features, and biological activity are also described.